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JAKE TAPPER, CNN ANCHOR: So, the Cuban people may now get Starbucks, but will they ever taste freedom?

I am Jake Tapper live from Havana, and this is THE LEAD.

The world lead, stars and stripes over Cuba. The United States reopens an embassy that still had calendars on the walls from 1961. We are live in Havana, Cuba, with all of the developments on this historic day.

Of course, one American flag does not solve every problem or release the Castro brothers' grip on the people here. We will talk to some of those who have dared to speak out for democracy and have risked their lives in the process.

And the politics lead. So, we have a Clinton and we have a Bush. Why not complete this episode of I love the '90s with Al Gore? What does this new rumor about Gore running say about confidence in the Democrat who was supposed to be running away with the nomination?

Buenas tardes from Havana, Cuba. Bienvenidos to our viewers in the United States and around the world. I am Jake Tapper coming to you live outside the U.S. Embassy here in the Cuban capital on a day of history and a day of controversy.

The last time the American flag flew on the pole behind me was seven months before President Obama was born, January 1961. And President Dwight Eisenhower cut off diplomatic relations with this island nation, angered with Fidel Castro's cozy relationship with the Soviet Union and the repression of his people.

President Eisenhower said then -- quote -- "Our sympathy goes out to the people of Cuba now suffering under the yoke of a dictator."

The dictator and his yoke now enforced his brother, Raul, well, they outlived President Eisenhower, as well as President Kennedy and President Johnson and President Nixon, President Ford, and President Reagan. The embargo, too, that our government imposed on that regime, that lives on and that has not been lifted, but today, hoping that diplomatic relations will bring about change here, change where the previous policies did not, the president who was born not even when this all began is making a high-stakes bet.

And President Obama sent John Kerry today to Havana to become the first U.S. secretary of state to step foot on this island since 1945. And today here in Havana, Kerry tried to turn the page to a new chapter in U.S.-Cuban relations.

(BEGIN VIDEO CLIP)

JOHN KERRY, U.S. SECRETARY OF STATE: Clearly, the events of the past, the harsh words, the provocative and retaliatory actions, the human tragedies, all have been a source of deep division that has diminished our common humanity.

There have been too many days of sacrifice and sorrow, too many decades of suspicious and fear. That is why I am heartened by the many on both sides of the straits who, whether because of family ties or a simple desire to replace anger with something more productive, have endorsed this search for a better path.

(END VIDEO CLIP)

TAPPER: So, now here we are, the American flag now flying freely in this land that is still decidedly not free.

Cuba still cracks down on dissidents. Just days ago, the regime here arrested 90 people protesting Castro's iron grip. And it's for reasons like this that critics claim that today only will give legitimacy to a dictator who has no interest in true change.

Earlier, I spoke with three senators who hope that's wrong, Republican Jeff Flake, Democrat Amy Klobuchar, and Democrat Patrick Leahy, members to U.S. delegation in Havana today. I asked them, what are they doing to assure the Cuban people that this new era will not just reward the communist-run government.

(BEGIN VIDEOTAPE)

SEN. PATRICK LEAHY (D), VERMONT: Well, I think the people of Cuba feel it will be good for them.

That's why so many -- I have been here several times this year -- will come up wearing T-shirts with American flags on it and say it's about time.

Is it going to be perfect? No. Will it be better than it has been? Yes. And it is going to require some getting used to by both the United States and Cuba, but it's going to be better for the people of Cuba. That's why I and the others have fought so hard for it. We fought that hard because we wanted it for the people of Cuba.

TAPPER: Senator Flake, I don't need to tell you a lot of your fellow Republicans are very, very wary of this step today. Why are they wrong and how did you come to occupy this unique position in your party?

SEN. JEFF FLAKE (R), ARIZONA: Well, there are -- I should note there are a number of Republicans who have been working on this policy. I am not alone. I am the only one here, but there are a lot of Republicans who have been working on this.

[16:05:07]

And I would say, for those who are opposed, just like Pat said, it's not going to be perfect, but the issues where we still have grave concerns on human rights and democracy issues, we will be far better able to press those issues with diplomatic relations and with increased travel and contact with Cuban people. So, it's a good step.

TAPPER: And you were speaking to some butter industry individuals in Minnesota who are excited about this. Why were they excited about this?

SEN. AMY KLOBUCHAR (D), MINNESOTA: Well, I don't know how their butter will survive in this heat.

TAPPER: I'm barely surviving.

(CROSSTALK)

KLOBUCHAR: But I think the point is that this is going to open up markets for U.S. businesses as well once we establish these relations this historic day today, but the next step is to lift the travel ban, so Americans can come, and then lift the embargo, which we are all working on, so that we can finally get some American goods coming into Cuba, and I think that would be good for everybody.

TAPPER: What is the likelihood, Senator Leahy, that the embargo will be lifted? It can only be done by Congress. It can't be done by President Obama unilaterally, as you know.

LEAHY: If the question of the embargo was put to a vote of the whole country, it would be lifted immediately.

The vast majority of Americans, Republicans and Democrats alike, want it lifted. Those who say stand tough, and those Castros will be gone, they gave the same advice to President Eisenhower, Kennedy, Johnson, Nixon, and everybody else. It has not worked. Let's try something new.

TAPPER: Senator Flake, there are cynics out there who say this is all around, beyond President Obama wanting something in his legacy, this is about business, this is about Americans wanting to make money, rich Americans wanting to make more money, and it's not about the people of Cuba.

What is your response to those cynics when they say that to you?

FLAKE: Well, that's not it at all.

When Americans travel here, increasingly, they are staying at a bed and breakfast or private homes. They're eating at private restaurants. The number of Cubans that are working outside of the state has increased exponentially just in the last couple of years. So, that benefits the average Cuban, not the government.

And so that's a good thing. As more business comes here, as the infrastructure -- they need investment, let's face it. In order to get investment, they are going to have to make changes, going to have to have more transparency, rule of law, rights to contract. That will come and that will be good for Cubans.

TAPPER: But you must be concerned, Senator Klobuchar, because I know you, as well as the other senators here, are very concerned about human rights issues. And when you hear that somewhere between 90 and 100 dissidents, protesters were arrested just a few days ago, that must fill you with at least some ambivalence about this move, although I know you are very in favor of it.

KLOBUCHAR: Well, I think, Jake, we know this has been going on for years. And the same old policy has not changed things.

So, this idea that we have an embassy where finally our personnel can travel more freely, meet with these dissidents -- the pope is coming here, and, certainly, he's going to have a human rights message. And I think the other thing about this is, there's a lot of poverty here. And I know a lot of Americans want to come and see these beautiful buildings and these beautiful old cars.

But we have to remember there is nothing romantic about poverty. And the way you lift people out of poverty and the way that you tackle these human rights abuses is by exposing people to entrepreneurship and a new culture and moving on from here.

TAPPER: Senator Leahy, one of the things that I have heard some advocates of today's move argue is, the excuse that the Castro brothers have as to why this country is the condition it's in will be gone once the diplomatic relations are established and the embargo is gone. Then really the blame lies at the feet of the Castro brothers. Do you agree with that?

LEAHY: Yes.

I think it was about 15 years ago Marcelle and I were having dinner one night with Fidel Castro. He started in about the -- our embargo. And I said, "Heck, the embargo is the best thing you have got going for you."

He said, "What do you mean?"

I said, "As it is now, you have got a failed economic, failed political system. You can blame it all on us."

He gave me a look, turned to my wife, who is a registered nurse, said, "I will talk to you. You are the humanitarian."

The United States has an enormous amount to offer in human rights, and in freedom of speech and the ability to move students, and all of these things can be so helpful to them. Let's get rid of the excuse of the embargo, because that's simply an excuse to say no, when the Cuban people want to say yes. FLAKE: I have always thought, if you want to punish the Castros, make

them deal with spring break once or twice.

(LAUGHTER)

TAPPER: We will leave it there exactly on that note. My mind is racing.

Senator Leahy, Senator Flake, Senator Klobuchar, thanks so much. I know you have a lot of things to do. We really appreciate it.

LEAHY: Thank you.

KLOBUCHAR: Thank you.

(END VIDEOTAPE)

TAPPER: as today marks a new beginning between the United States and Cuba, others are not so hopeful. They do not expect change anytime soon, at least not change for the better. They are showing us some of the restrictions still in place after decades of oppression.

[16:10:00]

That's next.

(COMMERCIAL BREAK)

TAPPER: Welcome back to THE LEAD. I am Jake Tapper, coming to live from Havana, Cuba.

Let me just show you one thing that we have here that is very interesting. The U.S. Embassy here, back when it just was the U.S. Interests Section, they used to have a news ticker providing information on the side of the building. Then the Cuban government retaliated by putting up a bunch of flags, these dozens and dozens of flags. They're not up anymore, but they were up to block the view so the Cuban people could not read the news ticker.

They were very loud in the wind here by the beachfront. So the U.S. Interests Section and the Cuban government came up with an agreement. The flags would come down if the news ticker would come down, so, these flagpoles, which only have one flag now, the Cuban flag, something of a monument to past censorship and annoyance, diplomatic annoyance.

But let's talk more. The two countries here that have spent the last half-century as arch enemies obviously took a major step today in normalizing relations, but we can't forget, amidst all the pomp and circumstance, there are many dissidents here on the island who believe that their day-to-day lives are filled with economic hardship and oppression and human rights abuses, that that's not going to change.

(BEGIN VIDEOTAPE)

TAPPER (voice-over): Not everyone here is celebrating. Antonio Rodiles is part of the pro-democracy dissidence community, a rare and brave vocal critic on the island who dares to criticize the Castro government.

He's not only spoken out himself for years, he has hosted the dissidence community at his family home.

TAPPER (voice-over): Their campaign for greater freedom here has come at a significant cost. Rodiles and other activists are routinely rounded up and arrested as they try to make their way to mass at a local Catholic church. Women there dressed in white called Las Damas de Blanco bear silent witnesses to their husbands serving jail time as political prisoners.

(on camera): And how did they treat you? Does the government retaliate against you?

RODILES: Yes, they've been repressing a lot. They used to organize like a kind of police operations around the house to arrest the people that were -- they were coming here.

TAPPER: Just for what? Just for coming?

RODILES: Yes, exactly, because they don't want that kind of activities.

TAPPER: Have they ever done anything to you? Have they arrested you? Have they physically hurt you?

RODILES: Yes, I have been arrested several times, and also I have been beaten. I have been in jail for certain days, and both in the last time the situation has been changing for worse.

TAPPER: It's getting worse?

RODILES: Yes.

TAPPER (voice-over): This is what happened in July when Rodiles was arrested on his way to church, put in the back of a police car and beaten with handcuffs.

(on camera): President Obama and Secretary Kerry, they argue, look, we have tried it with an embargo and blockade for decades and nothing has changed. Maybe by doing this, there will be more human rights and democracy in Cuba. Do you agree with that?

RODILES: I do not agree. We really are upset because the American government doesn't want to put any pre-condition for that political process, and the Cuban government is taking a lot and they are not giving anything.

TAPPER (voice-over): As the American flag rose over the U.S. embassy in Havana today, there were no dissidents there, none on embassy grounds. Instead, Rodiles said he and others have been invited to a private ceremony with the secretary of state at the ambassador's residence in the afternoon, but he declined their invitation.

(on camera): Do you think Obama and Kerry doing this hurt the cause of people like you, people fighting for freedom?

RODILES: Sometimes, yes, because first, the government has more legitimacy in the international community. They feel more free to repress us. But at the same time, the signal for the people fighting the government, making a huge confusion, because right now, people don't understand who are their friends that are supporting the changing for democracy, who are the people supporting their government.

(END VIDEOTAPE)

TAPPER: Even though so much here seems stuck in 1961, there are some small yet historic changes, some that you and I might take for granted. Last night, I asked our Havana bureau chief Patrick Oppmann to help demonstrate one of those changes.

(BEGIN VIDEOTAPE)

TAPPER: One of the most disconcerting things for a wired American such as myself here in Cuba is that there is no Internet, not when you land at the airport, not at the hotel, certainly not walking down the street. But we are right now at one of these new Wi-Fi hot spots that the government has set up in the last few weeks, and, yes, you can see Cubans are gathering and logging on.

What am I supposed to do with this, Patrick?

PATRICK OPPMANN, CNN HAVANA BUREAU CHIEF: So, you buy the card, and the way you're supposed to do is you are supposed to go through a government office, sign a form very likely saying you are not going to put any counter revolutionary activities, pay $2, or you can come here, buy to the black market for $3, put in the code, you are online. You are chatting with relatives you haven't seen in years. They're all night surfing the web. They have never been able to do this in their lives and look, they're loving it.

TAPPER: It's incredible. It's incredible. The crowd would never be this crowded?

OPPMANN: This park used to be empty and it's full here.

[16:20:00] Cubans are joining a long last Internet revolution.

TAPPER: And, of course, the black market salesman, a new career that just started a few weeks ago here in Cuba.

We will have much more from Havana, Cuba, right after this.

(END VIDEOTAPE)

(COMMERCIAL BREAK)

TAPPER: You're looking at pictures there at the Bay of Havana, Baia de Havana. I wonder what it's going to look like in 10 years.

Welcome back to THE LEAD. I'm Jake Tapper.

I'm live in Havana, Cuba, where earlier today, after 54 years, the U.S. flag, the American flag, was raised at the newly re-opened U.S. embassy.

Coming up, we will have much more about this historic and controversial day, the moving ceremony, what it might mean for you and for both countries going forward.

[16:25:01] But, first, let's talk about the United States and the politics lead with Hillary Clinton's e-mail server now in the hands of the feds. Today, Mrs. Clinton woke up to chatter about yet another possible challenge for the Democratic presidential nomination, and it is looking less and less like a lock each day.

CNN senior Washington correspondent Jeff Zeleny is live for us in Clear Lake, Iowa.

Jeff, I woke up this morning and I heard this. Al Gore?

JEFF ZELENY, CNN SENIOR WASHINGTON CORRESPONDENT: Jake, you're right, there has been some chatter in Democratic circles about Al Gore. Will he get in?

But I can tell you, the chatter here in Clear Lake, Iowa, is about the Democrats in the race, a lot of people from Martin O'Malley supporters here, and Hillary Clinton as well, all Democratic candidates gathering here tonight on the same stage, it's a reminder there still could be yet another wrinkle in this Democratic race.

(BEGIN VIDEOTAPE)

ZELENY (voice-over): Tonight, the field of Democrats will take the stage in Iowa. There's Hillary Clinton, and Bernie Sanders, and Martin O'Malley and more. But other hopefuls may still be waiting in the wings.

Vice President Joe Biden called more supporters today. He's asking advisers to start making a plan if he decides to run.

Even friends of Al Gore wonder if he should jump in, a suggestion his spokeswoman quickly shot down. Never mind Bush//Clinton, but a Bush/Gore rematch?

ZELENY: At the Democratic booth at the Iowa state fair, it was the topic of conversation.

(on camera): We have something for Hillary Clinton, Martin O'Malley, Bernie Sanders, Jim Webb, is there room for another person in the race, do you think?

JOHN NEIDERBACH, IOWA DEMOCRAT: Oh, I think it's -- well, look at the Republican side. Obviously, I hope we don't get to that level but there's always more room. Several people say they hope Joe Biden jumps in. It will give them a good choice. It will give more depth. I'm truly undecided.

ZELENY (voice-over): Clinton holds a wide edge in Iowa, leading Sanders by 19 points. But not all Democrats are convinced she's the one.

BECKY DANILSON, IOWA DEMOCRAT: I'm not sure, I -- I don't know. As much as I would like to see a woman in there, definitely, I don't know about her being the one.

ZELENY: O'Malley is trying to win over voters one by one, taking time out to hit the giant slide with two of his kids.

(on camera): You are very optimistic that in six months, voters are still open minded of your candidacy.

MARTIN O'MALLEY (D), PRESIDENTIAL CANDIDATE: I am. There's not a doubt in my mind that people are looking for a new leader. And after we get done rolling around in our summer of anger here, people are going to look at the candidates and evaluate which of us is a new perspective of a new generation that can actually govern and get things done.

(END VIDEOTAPE)

ZELENY: Now, Governor O'Malley certainly believes that he is the candidate of the future. We heard a lot of his supporters behind me here. But it's important to remember, Hillary Clinton still has a strong lead in Iowa. She got an endorsement from former Senator Tom Harkin, but, Jake, half of the voters here are still undecided -- Jake.

TAPPER: Jeff Zeleny, thanks so much.

On the Republican side, today, it was Jeb Bush's turn to convince Iowa voters he's fully committed to competing there as polls show many Iowans seem to be giving up on him. Today is the last chance for the candidates to make their pitches before they all get Trump tomorrow. Tonight, Donald Trump is holding a rally in New Hampshire before heading to Iowa.

Sunlen Serfaty is today's CNN Trump correspondent, live for us in the Granite State of New Hampshire -- Sunlen.

SUNLEN SERFATY, CNN CORRESPONDENT: Jake, the Trump campaign really does seem to be digging in deeper in that early states, like here in New Hampshire. Donald Trump, this afternoon, will meet with state activists and then hold a campaign rally. But, tomorrow, he'll also try his hands at retail politicking in Iowa.

You know, these small shifts in his campaign strategy come as he is set to make his Iowa landfall tomorrow.

(BEGIN VIDEOTAPE)

SERFATY (voice-over): Riding high in the polls, Donald Trump will make a dramatic landing. On Saturday, Trump will fly in on his trademark helicopter for his trip to the Iowa state fair. Sources say he will take supporters up for free rides.

And while it may all seem like fun and games, there are small signs Trump may be trying to mount a more serious campaign, beefing up staff in Iowa, laying groundwork for a potential longer campaign, and promises for policy specifics.

But when asked today for some of that substance, Trump said not yet.

DONALD TRUMP (R), PRESIDENTIAL CANDIDATE: I don't do a plan. I go in and get it. Too much talking and not enough action.

SERFATY: Meanwhile, a much more reserved entrance today in Iowa for Jeb Bush.

BUSH: I like the way we did it. We went from the Hampton Inn right across the street and walked in here.

SERFATY: Still trying to find his own footing. His brother's legacy continuing to cast a wide shadow, continuing to trip him up on the trail. After finally saying he wouldn't have gone into Iraq based on today's facts, Bush is now saying this.

BUSH: I'll tell you, though, that taking out Saddam Hussein turned out to be a pretty good deal.